“Logic will get you from A to B. Imagination will take you everywhere.” – Albert Einstein
I remember the first time I heard about Dr. Timothy Cottrell joining ‘Iolani. It was a balmy summer morning, and the campus buzzed with anticipation—new faces, new ideas, and a fresh sense of possibility. But behind the calm Hawaiian sun, Dr. Cottrell was juggling two worlds: wrapping up his final months at The Harley School in Rochester, New York, and preparing to lead a school with more than 1,800 students and a 150-year history. Imagine that kind of transition—almost 5,000 miles away, across oceans and cultures. Yet somehow, he made it look effortless.
From Rochester to Honolulu: A Journey of Vision and Imagination
Dr. Cottrell’s story isn’t just about moving from one school to another. It’s about a life threaded with curiosity, rigor, and heart. At The Harley School, he transformed the campus through visionary initiatives: from founding the Center for Mindfulness and Empathy Education to forming partnerships that advanced sustainability, to helping construct a “living building” with a socially-driven curriculum. His leadership wasn’t just about numbers or awards—it was about cultivating purpose and community.
His academic journey mirrors that same balance of logic and creativity. A B.S. in Chemical Engineering from Syracuse University, followed by an M.A. and Ph.D. from Princeton, might suggest a scientist strictly in the lab. But Dr. Cottrell’s imagination led him into teaching, tutoring, and eventually creating award-winning educational software. Logic and creativity, hand in hand.
The Right Fit for ‘Iolani
When the school began its search for a new Head in 2011, it wasn’t just about credentials. Vision, leadership, cultural understanding, and spiritual commitment were key. After a meticulous process involving faculty, students, alumni, and parents, Dr. Cottrell emerged as the unanimous choice.
Ann Yoneshige, Interim Dean of Upper School, recalls: “He believes in a very community-based school. He’s a wonderful communicator and listener. He has vision and knows how to turn it into reality.”
And indeed, it’s that combination of hands-on approach and big-picture thinking that defines his style. He doesn’t just delegate; he engages, teaches, and mentors, all while balancing the joys and demands of family life with his wife Lisa and their two sons.
Lessons from a Life of Learning
Growing up around racehorses in Geneseo, New York, instilled in him an early work ethic. Long days grooming horses, attending county fairs, and observing his father’s dedication taught him resilience and diligence. “At the core, I consider myself a values-based leader,” he reflects. And those values have guided him through every stage of his career—from tutoring high school students at Princeton to launching a tech startup, to leading schools where every student matters.
Even now, at ‘Iolani, he keeps his door open to students, sharing cookies on the campus lawn and listening to their stories. Whether it’s snowboarding, surfing, or fishing, Dr. Cottrell brings the same energy and curiosity into life outside the classroom as he does inside.
People Make Schools
Ask him what makes a great Head of School, and his answer is simple: people. Strong one-to-one relationships, a community that thrives on passion for learning, and leadership that empowers everyone. He sees schools as ecosystems where each individual contributes to a larger purpose. Communication, mentorship, and empathy are as important as vision and strategy.
“New growth always occurs with the special flavor and characteristics of the institution,” he notes. “You have to interpret ideas through the lens of the school to make them alive.”
Dr. Cottrell also believes in giving back. Education isn’t only about academic excellence—it’s about cultivating global citizens who engage with the world and their communities meaningfully.
Advice and Reflection
Dr. Val Iwashita, the previous Head, offered a piece of guidance: “Be your own man.” It’s advice that resonates with Cottrell’s approach: balancing personal values with professional responsibilities, listening deeply, and ensuring that every decision honors both tradition and innovation.
As the ‘Iolani community welcomes him, one thing is clear: Dr. Timothy Cottrell is more than a leader. He’s a mentor, a listener, a visionary, and most importantly, someone who reminds us that logic takes us far, but imagination truly takes us everywhere.
And in Honolulu, under the Hawaiian sun, it seems the journey has only just begun.